Friday Night with Tom Brady and Guy Fieri

At a charity event in Boston, the most hated man in football and the perpetual punchline of the food world came off like, well, really awesome guys.

If you can think of something more quintessentially "Massachusetts" than Tom Brady throwing a football to a Kennedy at Harvard, I'd love to hear it. Maybe Ben Affleck drunk on Harpoon fist-fighting a cousin at an Aerosmith concert?

Dressed in khakis and bright red sneakers, America's Public Enemy No. 1 was throwing footballs again Friday night. Or at least, it seemed like he was. From my vantage on the opposite side of the field, cordoned off with the rest of the media, away from the crowd and the participants like we'd been banished to a distant island, one could sort of make out Tom Brady rifling passes. His targets were a team of New England Patriots past and present, local celebrities and politicians, sponsors, and beneficiaries of the Best Buddies organization in whose honor this exhibition touch football game at Harvard Stadium was being held. If the glaring, early evening sun cooking down on the media horde was meant to be received as a metaphor, it wasn't lost on us. Tom Brady does not particularly consider us his friends these days. You can hardly blame him with the way the NFL great—and, okay, as a Bostonian, probably best to come out and say it: one of my personal heroes—has been dragged through the mud over Deflategate. (Then back over again just to make sure the job was done.)

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The event was part of Best Buddies Challenge, an annual fundraiser for Best Buddies International, the organization founded by Anthony Kennedy Shriver, of, you know, the Massachusetts Kennedy Shrivers, to help people with intellectual and developmental disabilities. The program pairs volunteers with a buddy for whom they serve as a mentor. The football game and "tailgate party" hosted by Guy Fieri after the game are an annual kick off to the weekend's 100 mile fundraising bike ride from Boston to Hyannis Port.

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Brady served as the QB for four teams, with rotating lineups that included the likes of Governor Charlie Baker, congressman Joe Kennedy III, Dane Cook, and Patriots players like Julian Edelman, Danny Amendola, and Rob Ninkovich. While the game was clearly all in good fun, every so often, as you watched Brady go through his reads, consider a waving youngster calling for the pass, then move on until he found an open receiver, there were moments when his famed competitiveness reflexively kicked in. At one point, Dane Cook picked him off and took the ball back the other way for a touchdown, which is a hilarious sentence to write (and appeared to burn Brady a little). Edelman and Amendola, in particular, seemed to revert into their standard piston-pumping modes as well, particularly when matched up against each other. I couldn't help but worry someone was going to get hurt out there. Never mind the children, I was just hoping it wouldn't be Brady.

Luke O'Neil

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At halftime, I snuck my way past security over to the players' side. Sidling up to Dan Koppen and Christian Fauria, two former Patriots, seemed like a good idea at the time, until I was confronted by their palpable immenseness. It's always a strange feeling standing next to a professional athlete who could squash you like a bug, almost like spotting a bear in the woods, albeit a bear coached in the dark art of media relations by Bill Belichick. I asked Koppen what he thought about the two receivers going at it. "I think there's a competitive spirit between those two, and when they're out playing against each other, the juices get flowing," he said, shortly before I was promptly ushered away.

Over on the sideline, things were more magnanimous. A phalanx of Miss USA and Miss Teen USA competitors meandered around snapping photos with kids, while Guy Fieri held court. Lauren Baker, the First Lady of Massachusetts, was effusive in her praise of Best Buddies. "This is an unbelievable organization that provides an incredible service to kids who—really—look at the smiles on their faces," she said. "This is so huge. They've touched the lives of thousands of kids, and when you can see it all in one place, it's really unbelievable."

Steve DiFillippo, owner of Davio's Northern Italian Steakhouse, who, along with Fieri, arranged the postgame dinner, donating much of the food and staff from his restaurants, was beaming. "I caught two passes, so I'm good for the rest of my life," he said. "Two passes from Tom Brady? Are you kidding me? When it was coming to me in the air I was like, you'll probably never get this opportunity again, so don't drop it." The group is nearing $6 million in its fundraising efforts this year, one million over its stated goal, he said. "These kids have so much spirit, and to be around them, it's actually great for me. It's just so refreshing how hard they work."

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The governor, a former longtime Big Brother, would soon be making a backstage costume change from his suit to jump into the game, where his long frame certainly helped him stand out in traffic, has been involved with the event for about 10 years, even taking part in the bike ride a few times. "First of all, I think they've come up with a very special way of engaging the larger public and creating events that raise attention and awareness for kids with developmental disabilities," he said. "The idea of creating mentors and people who can sort of serve as advisors and supporters for folks who are developmentally disabled is just a great cause and a great idea."

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Hard to argue with any of that, of course, but I wanted to get him on the record for a different sort of cause that seems to be on many New England minds these days: Where does he stand on the #FreeBrady campaign? "I'm hoping that, come the fall, it's all going to be about playing football," he said with a laugh. What if it isn't though? Could he use his office to enact some sort of pardon? "I don't think he's going to need any help from me!"

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The only face that seemed more enthusiastic on the sidelines than the buddies was Fieri, who has been a long time participant of the event, and helped corral a team of Boston's best chefs for the event. "Brother, you have stumbled upon one of the greatest charity events," he gushed. Fieri has played in the game for the last five years, but was sidelined this year with plantar fasciitis. "Ever had that? It's a nightmare, dude."

Just a few years ago, Fieri was outside the game at a grill with some friends passing out appetizers to people as they walked by, but it's grown immensely since then, he said. "It's great, not just because of the money that's raised, but because of the awareness that it brings," he said. "I gotta tell you something: Shriver is a genius, Brady is incredibly generous. All the players that come out, all the celebrities that come out, everybody gets behind us." It's easy to be snarky about Fieri, but, even as a cynic who's not easily charmed by famous people, he stood out as one of the most sincere and genuine celebrities I've ever met. We chatted at length over the course of the night, including about the late Esquire food writer Josh Ozersky. Fieri eagerly stopped to pose for photos with anyone who asked—and they all asked.

After the game, Fieri's tailgate party (more like a charity dinner), winnowed down the crowd in the stands to VIPs and donors. Media were, again, decidedly unwelcome, but a friendly staffer managed to sneak me in around the back. Inside, guests dined on tuna tartare with ginger sorbet, short rib tacos, and an elaborate spread from Davio's and company. Shriver served as emcee, exhorting the spirit of the buddies, who joined him on stage.

"The reason we're here tonight, and the reason I've been at this for 25 years, is because of this guy right here," he said, gesturing to a buddy named Ben. "I just feel so fortunate to be here and to be part of this guy's life, and to part of this organization that ensures that this guy has every chance that my son does. These two guys should do everything in life equally."

It was all about the kids, as they say, but there was one person whose presence seemed to dominate the night. Brady, who drove himself from inside the stadium to the adjacent auditorium about 100 yards away while throngs of fans waved and pawed at his car, took to the stage to toss footballs into the dining room. Each person who waved for one had to pledge $1,000 if they caught it. "This is one of the highlights of my year," he said, in what were his first public comments since he announced he was still "digesting" the Deflategate report.

"It's all about the buddies; it's always about the buddies," he said. "Friendship is an important part of our lives, especially when you go through challenging times. It's great to have as many friends as you can."